Neither are a relationship killer, unless they can't be resolved.

I'm assuming you got this resolved by now, but I posted to help anyone else that might have that same question.

My only concern is whether it's compatible with the newer versions of qb (I use Pro 2015).Your site only mentions that it works with 2012 and 2013.  

(If someone like myself is involved from Design/Partnership Role, we could possibly squeeze out some value from this.)San Jose has a General Plan, most likely your R-M is now in Neighborhood Residential Designation, so you must prove your density is compatible with existing neighborhood pattern (50% of properties on your block meet or exceed your proposed density)Let me know if you want to talk off line!

Should I just let the property stay with the management company for now, let them handle all the rent collection and any issues/calls while I work on getting the crawlspace issues resolved.  ...Or do I self-manage, and get the learning experience of being a landlord.  

If the maintenance issues could be resolved, that's potentially ~$2,000 more in annual profit.

I didn't know if the exterminator would cover me to show an effort that we tried to resolve the issue or if we can just do traps.

You will be nothing special to them, and they will not have any sense of urgency to resolve your issues with problem residents, screwed up payments, etc. 

Which is why I really suspect there's a difference in values here that's not going to be resolved without further discussion. 

What I mean to say is, does she need cashed out because she has some financial burden that must be resolved?